Red tetrazo dye.



nn'rnnr orrion KARL JEDLICKA AND ARNOLD SCHEDLEIQ OF BASEL, SWITZERLAND, ASSIGNOR TO THE FIRM OF SOCIETY OF CHEMICAL INDUSTRY IN BA SLE, OFVBASEL, SWITZERLAND.

Specification of Letters Patent.

Patented May 26, 1908.

Application filed May 14:, 1907'. Serial No. 373,632.

' of an azooxyamin of the formula:

pennin \l I=R-NH (where It represents the rest of an aromatic radical, such as C T-I C,,I-I .CH C,H .0CH GGIIQ(CH3)2 etc,) with two equal or different molecules of amidoarylacidyl-amidonaphtholsulfonic acids of the general formula:v

wherein It has the same signification as above.

The dyestuffs which may be obtained in this way constitute in dry state red to reddishbrown powders whiclh dissolve in water with yellowish-red to bluish-red coloration and dye unmordanted cotton clear, orange-red to bluish-red tints. By diazotation on the fiber and subsequent development with betatrated hydrochloric acid and diazotized; while cooled by ice, with 14 kilos of sodium nitrite, whereupon the tetrazo-solution is poured into a solution of 88 kilos of meta amidob enzoyl-2-amid0-5-naphthol-1 7-disul fonic acid and 80 kilos of sodium carbonate. Tlie combination is finished after a short time the mass is then heated to C., a small quantity of common salt is added thereto and the dycstuff is filtered, pressed and dried. The thus obtained dyestufi constitutes a yellow-brown powder which dissolves in water with an orange color.. When dyed directly upon unmordanted cotton it yields orange-red tints; when diaz'otized on the fiber and developed withbeta-naphthol the said tints turn to a deep yellow-red very fast to washing.

. When in the foregoing example the azoxyanilin is replaced by meta-azoxytoli'iidin, a dyestufi' is obtained which dyes unmordanted cotton scarlet-red shades,v the vividness of, which increases by development on the fiber with beta-naphthol and which simultane: ously become absolutely fast to'washing. The meta-oxyanisidin gives a blue-red dyestuff.

' If instead of ineta-amidobenzoyl-Z :5-amidonaphthol-lfl disulfonic acid other amidoarylaoidylamidonaphtholsulfonio acids are employed, such as for example the metaor para-'amidobenzoyl derivatives of the 2:5 amidonaphthol-7-monosulfonic acid, of the 2:8-amidonaphthol-6-sulfonic acid, of the 2 :8-amidonaphthol-618-disulfonic acid and of the 1:8-amidonaphthol-3:6-disulf0nic acid, three are obtained dyestuffs of similar properties.

Example II: 12.8 kilos of azoxytoluidin' (obtained from ara-nitro-ortho-toluidin) are diazotized in t 1e usual Way and'ra idly poured into a common solution of 22 ki os of meta amidobenzoyl 2 amido 5 -naphthol- 1 :7'-disulfonic acid and 18 kilos of'metaamidobenzoyl -2 amido 8 -naphthol 6 sulfonic acid in 40 kilos of sodium carbonate. The dyestuff separated in the usual way by heating, salting out, filtering and dyeing forms a brown-red owder. It dyes unmordanted cotton bluis 1-16d. tints which by diazotation on the fiber and development with betanaphthol'turns to a scarlet-red.

Instead of pouring, as in the foregoing example, the tetrazo compound directly into a solution of a molecular mixture of two different amidoarylacidyl derivatives, it is obviously possible to proceed in such a way that it is first coupled only with'one molecule of an 'amidoarylacidyl amido --naphth0lsulfonic acid whereupon the resulting intermediate product is brought to react with a sec- 0nd molecule of an amidoarylacidyl derivative.

In an analogous manner we proceed for the manufacture of diazo dyestuffs by using other azoxyamines and other amidoarylacidylamidonaphtholsulfonic acids.

.What We claim is:

1. The herein described manufacture of red tetrazo consists in combining one molecule of the tetrazo-derivative of an azoxyamin with two molecules of' amidoarylacidyl amidonaphtholsulfonic acids of the general formula:

gI II=CO.R-NH

roces s for the 'estufls, which (where R represents the rest of an aromatic radical).

2. The herein described process for the manufacture of red tetrazo-dyestuffs, which consists in combining one molecule of a tetrazotized azoxyamin with ,two molecules of amidobenzoylamidonaphtholsulfonic acids.

3. The herein described process for the manufacture of tetrazo-dyestuffs, which consists in combining one molecule of a tetrazotized azoxyamin with two molecules of metaamidobenzoylamidonaphtholsulfonic acids, one at least of the said two molecules being a molecule of meta-amidobenzoyl-2-amido-5- naphthol-l :7-disulfonic acid.

4. As newproducts', the tetrazo-dye'stuffs (where R, R and R signify rests of aromatic radlcals), formin in dry state red to reddish-brown owc ers soluble in water with yellowish-rec to bluish-red coloration and dyeing unniordanted cotton orange-red to bluish-red shades which, when further diazotized on the fiber and develo ed. with betanaphthol, yield Valuable rec tints fast to washing.

In witness whereof we have hereunto signed our names this 1st day of May, 1907, in the presence of two subscribing witnesses.

KARL JEDLICKA. ARNOLD SCH EDLER.

Witnesses GEO. GIFFORD, AMAND BITTER. 

